Hike Description:

From the kiosk at the end of the parking area, bear right and proceed ahead on the red-blazed Duggan Trail. In about half a mile, the red trail ends at a junction with the blue-blazed Reservoir Trail. Continue ahead on the blue trail, which immediately crosses Ben's Bridge (a wooden footbridge) and climbs along a picturesque stream, with cascades and waterfalls, following an old woods road. In half a mile from Ben's Bridge, you'll notice a pipeline crossing the stream. A short distance beyond, the white-blazed Honey Hill Trail crosses. The grade now moderates, and the blue trail soon ends at a junction with the yellow-blazed Stillman Trail. Bear right and continue ahead on the Stillman Trail.

Soon, the Stillman Trail reaches the dirt White Oak Road. Here, it is joined by the teal-diamond-blazed Highlands Trail, which comes in from the left. The joint Highlands/Stillman Trails now turns right and follows the road for 100 feet, then turns left and begins a steep climb of Mt. Misery on a footpath. At the top, you’ll pass a radio repeater station and reach a limited viewpoint to the west and northwest, which is partially obscured by trees. Continue ahead for a short distance, and you’ll come to a much better viewpoint, with Black Rock Mountain visible directly ahead. You’ll want to stop here for a few minutes to savor the view and take a break from your arduous climb (you’ve climbed nearly 700 feet from Ben’s Bridge).

Continue ahead on the yellow/teal diamond trail, which begins its descent of Mt. Misery, first gradually and then more steeply. In a rocky area at the base of the descent, you’ll notice a triple white blaze, which marks the start of the Scenic Trail. Turn left and follow the white-blazed Scenic Trail, which crosses the blue-blazed Swamp Trail at the end of the rocky area and begins a steady climb of the Hill of Pines, passing through attractive mountain laurel and hemlock.

At the top of the climb, the trail comes out on open rocks, with a spectacular west-facing view. Black Rock Mountain may be seen on the right, and the Black Rock Forest fire tower is to its left. (Despite the name "Hill of Pines," there are only two pine trees near the summit, which is mostly covered with oaks). You’ll want to spend some time at this magnificent vantage point.

The trail climbs a little to the true summit and then descends the hill. After a relatively level section, it crosses the dirt Carpenter Road diagonally to the right. It now begins a gradual climb of Rattlesnake Hill. After descending a little, the trail levels off, then resumes its climb. Soon, a short side trail on the right leads to a viewpoint from a rock ledge adjacent to a large pine tree. The fire tower may be seen straight ahead, and Bog Meadow Pond is to the left. Just ahead, the trail makes a short but steep descent. After a relatively level stretch, you’ll reach a second viewpoint – this one marked by a cairn and a gnarled, nearly horizontal pine tree. Continue ahead through a dense mountain laurel thicket and climb to the third viewpoint on Rattlesnake Hill, which offers a panoramic view from open rocks. Bog Meadow Pond is below on the left, with the rolling hills of Orange County beyond.

After pausing to enjoy the view, continue ahead on the white trail, which begins to descend, first steeply, then more gradually. The trail briefly runs along the southern boundary of Black Rock Forest, with Bog Meadow Pond visible through the trees to the left. After crossing the inlet stream of the pond, the trail reaches the dirt Bog Meadow Road. Turn left and continue along the road, which is marked with the white blazes of the Scenic Trail.

In a quarter mile, you’ll reach a junction with the yellow-blazed Tower Vue Trail, marked by a cairn and post on the right side of the road (this junction is just before a large rock outcrop). Turn right and follow the Tower Vue Trail over undulating terrain, through mountain laurel with an understory of blueberry. In about a third of a mile, there is a view through the trees of the fire tower from a rock ledge to the left of the trail. The trail now begins to run above Arthurs Pond, with views of the pond through the trees on the left.

When the Tower Vue Trail ends at the northern tip of the pond, by the dam, turn left onto the white-blazed White Oak Trail, cross below the dam, and continue along a gravel road. Soon, the White Oak Trail reaches Continental Road at a T-intersection. Turn right onto the road, continuing to follow the white blazes, but when the white blazes turn left and leave the road, proceed ahead on the road. Just beyond, you’ll come to a junction, marked by a huge white oak tree. Here you should continue ahead on Continental Road, as White Oak Road leaves to the right.

In another third of a mile, you’ll reach a complex intersection, with two yellow posts straight ahead (this intersection is designated as "Two Gates" on Trail Conference Map 113). Turn right, go around a gate, and continue on the yellow-rectangle-blazed Stillman Trail (also the route of the teal-diamond-blazed Highlands Trail). Just ahead, as the woods road bears left, bear right and follow the yellow and teal diamond blazes, which begin a gradual climb of Black Rock Mountain on a footpath.

After a short but very steep climb, you’ll reach the summit of the mountain (1,410 feet) amid scrub oak and pitch pines. The panoramic view from the summit includes Schunemunk Mountain and the Metro-North Railroad’s Moodna Viaduct to the west, and the Hudson River (crossed by the Newburgh-Beacon Bridge) to the northeast. On a clear day, you can see the Shawangunks and Catskills ahead in the distance. Again, you’ll want to take a break to appreciate the view – the broadest of the entire hike.

The trail turns right and descends gradually. With the wide White Oak Road visible ahead, the trail bears left and joins a woods road. A short distance beyond, follow the yellow and teal-diamond blazes as they turn right, leaving the road, and descend to Aleck Meadow Pond. At the pond, the trail bears left and runs below the dam, then crosses the outlet of the pond on a wooden bridge. Just beyond, turn left onto the white-blazed Honey Hill Trail. For the next quarter mile, this trail follows the route of an old pipeline. It then turns right and begins to climb, soon reaching a limited viewpoint marked by signs for "Aleck Meadow" and "Malley's Mill Bridge." After passing another radio repeater station, the trail begins a steady descent.

At the base of the descent, the Honey Hill Trail crosses the blue-blazed Reservoir Trail. A short distance beyond, the Honey Hill Trail crosses the covered Malley's Mill Bridge and ends at a kiosk. Bear left and continue on the wide Sybil's Path, which heads gradually downhill. As it curves to the right, it passes a north-facing viewpoint (marked by a bench). Continue to follow Sybil's Path to its end at the parking area where the hike began.